JP2015526441A5 - - Google Patents
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- Publication number
- JP2015526441A5 JP2015526441A5 JP2015527566A JP2015527566A JP2015526441A5 JP 2015526441 A5 JP2015526441 A5 JP 2015526441A5 JP 2015527566 A JP2015527566 A JP 2015527566A JP 2015527566 A JP2015527566 A JP 2015527566A JP 2015526441 A5 JP2015526441 A5 JP 2015526441A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- trifluoromethyl
- indazol
- benzoyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 59
- -1 hydroxycarbonyl Chemical group 0.000 claims 37
- 125000003545 alkoxy group Chemical group 0.000 claims 31
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 31
- 229910052736 halogen Inorganic materials 0.000 claims 31
- 150000002367 halogens Chemical class 0.000 claims 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 239000011780 sodium chloride Substances 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- FOCBRZYNWUYTNP-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(morpholine-4-carbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(=O)N2CCOCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F FOCBRZYNWUYTNP-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000001404 mediated Effects 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- CUJAFWQPUBJJEJ-UHFFFAOYSA-N 2-acetamido-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)C)=CC(C=2C3=CC=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 CUJAFWQPUBJJEJ-UHFFFAOYSA-N 0.000 claims 1
- RQBDVVCZSCAYQL-UHFFFAOYSA-N 3-(4-carboxyphenyl)-1-[2-chloro-6-(trifluoromethyl)benzoyl]indazole-6-carboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F RQBDVVCZSCAYQL-UHFFFAOYSA-N 0.000 claims 1
- FGSXFZVLHMWUDU-UHFFFAOYSA-N 3-fluoro-4-[1-(1-methylindole-2-carbonyl)indazol-3-yl]benzoic acid Chemical compound C=1C2=CC=CC=C2N(C)C=1C(=O)N(C1=CC=CC=C11)N=C1C1=CC=C(C(O)=O)C=C1F FGSXFZVLHMWUDU-UHFFFAOYSA-N 0.000 claims 1
- BPPONUKAAREGJL-UHFFFAOYSA-N 3-fluoro-4-[1-(2-methoxyacetyl)indazol-3-yl]benzoic acid Chemical compound C12=CC=CC=C2N(C(=O)COC)N=C1C1=CC=C(C(O)=O)C=C1F BPPONUKAAREGJL-UHFFFAOYSA-N 0.000 claims 1
- VWAYLDITYUHKSI-UHFFFAOYSA-N 3-fluoro-4-[1-(2-phenylpropanoyl)indazol-3-yl]benzoic acid Chemical compound C=1C=CC=CC=1C(C)C(=O)N(C1=CC=CC=C11)N=C1C1=CC=C(C(O)=O)C=C1F VWAYLDITYUHKSI-UHFFFAOYSA-N 0.000 claims 1
- URJOBDIUNWPXTR-UHFFFAOYSA-N 3-fluoro-4-[1-(naphthalene-1-carbonyl)indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=CC=CC=C12 URJOBDIUNWPXTR-UHFFFAOYSA-N 0.000 claims 1
- RQLYGRRZWKTFLU-UHFFFAOYSA-N 3-fluoro-4-[1-(oxolane-2-carbonyl)indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1OCCC1 RQLYGRRZWKTFLU-UHFFFAOYSA-N 0.000 claims 1
- AHXGVYIRKMKSAV-UHFFFAOYSA-N 3-fluoro-4-[1-(pyridine-3-carbonyl)indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CN=C1 AHXGVYIRKMKSAV-UHFFFAOYSA-N 0.000 claims 1
- FEMMZTXFLFEFMF-UHFFFAOYSA-N 3-fluoro-4-[1-[2-(2-oxopyrrolidin-1-yl)acetyl]indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)CN1C(=O)CCC1 FEMMZTXFLFEFMF-UHFFFAOYSA-N 0.000 claims 1
- UFMFURBJBPRJFN-UHFFFAOYSA-N 3-fluoro-4-[1-[3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-6-carbonyl]indazol-3-yl]benzoic acid Chemical compound C1N(C(=O)OC(C)(C)C)CC2C1C2C(=O)N(C1=CC=CC=C11)N=C1C1=CC=C(C(O)=O)C=C1F UFMFURBJBPRJFN-UHFFFAOYSA-N 0.000 claims 1
- MYRZEDFAAXWOCE-UHFFFAOYSA-N 4-[1-(1-benzofuran-7-carbonyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=C1OC=C2 MYRZEDFAAXWOCE-UHFFFAOYSA-N 0.000 claims 1
- HLQBLHMEGINUEZ-UHFFFAOYSA-N 4-[1-(2,3-dihydro-1-benzofuran-7-carbonyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=C1OCC2 HLQBLHMEGINUEZ-UHFFFAOYSA-N 0.000 claims 1
- ZQSOJGWWQMLPEG-UHFFFAOYSA-N 4-[1-(2,3-dihydro-1H-indene-4-carbonyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=C1CCC2 ZQSOJGWWQMLPEG-UHFFFAOYSA-N 0.000 claims 1
- KNXIOXOXYSMFDK-UHFFFAOYSA-N 4-[1-(2-bromo-3-chlorobenzoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC(Cl)=C1Br KNXIOXOXYSMFDK-UHFFFAOYSA-N 0.000 claims 1
- VQYAVXSWJIEBDY-UHFFFAOYSA-N 4-[1-(2-bromo-3-methylbenzoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC=CC(C(=O)N2C3=CC=CC=C3C(C=3C(=CC(=CC=3)C(O)=O)F)=N2)=C1Br VQYAVXSWJIEBDY-UHFFFAOYSA-N 0.000 claims 1
- BCDKQBWCSBECKY-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclobutylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CCC1 BCDKQBWCSBECKY-UHFFFAOYSA-N 0.000 claims 1
- CKFNTMBCGYATAC-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclobutylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CCC1 CKFNTMBCGYATAC-UHFFFAOYSA-N 0.000 claims 1
- RDQQWHRZYWLWJC-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopentylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CCCC1 RDQQWHRZYWLWJC-UHFFFAOYSA-N 0.000 claims 1
- RUPATPKYIMISQN-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoroindazol-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 RUPATPKYIMISQN-UHFFFAOYSA-N 0.000 claims 1
- ITAJZCHZGRGIEJ-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 ITAJZCHZGRGIEJ-UHFFFAOYSA-N 0.000 claims 1
- CSTNVZNXJBJIAB-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 CSTNVZNXJBJIAB-UHFFFAOYSA-N 0.000 claims 1
- AMQKIZZEIKBRFO-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 AMQKIZZEIKBRFO-UHFFFAOYSA-N 0.000 claims 1
- LMIWUTKCGKCAPR-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 LMIWUTKCGKCAPR-UHFFFAOYSA-N 0.000 claims 1
- NAJJOZBHQMYRCQ-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)pyrrolo[3,2-b]pyridin-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=CN1C(=O)C1=C(Cl)C=CC=C1C1CC1 NAJJOZBHQMYRCQ-UHFFFAOYSA-N 0.000 claims 1
- HYDRWUOWOHAYOO-UHFFFAOYSA-N 4-[1-(2-chloro-6-ethenylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C=C HYDRWUOWOHAYOO-UHFFFAOYSA-N 0.000 claims 1
- XQLORDGAAKKHJV-UHFFFAOYSA-N 4-[1-(2-chloro-6-methyl-4-morpholin-4-ylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC(N2CCOCC2)=CC(Cl)=C1C(=O)N(C1=CC=CN=C11)N=C1C1=CC=C(C(O)=O)C=C1F XQLORDGAAKKHJV-UHFFFAOYSA-N 0.000 claims 1
- MRUIGUAOGXKSOD-UHFFFAOYSA-N 4-[1-(2-chloro-6-morpholin-4-ylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1N1CCOCC1 MRUIGUAOGXKSOD-UHFFFAOYSA-N 0.000 claims 1
- STTDKBXVHRDKSV-UHFFFAOYSA-N 4-[1-(2-chloro-6-prop-1-en-2-ylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC(=C)C1=CC=CC(Cl)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 STTDKBXVHRDKSV-UHFFFAOYSA-N 0.000 claims 1
- SZTKTFVKDORSMX-UHFFFAOYSA-N 4-[1-(4-amino-2-chloro-6-methylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC(N)=CC(Cl)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 SZTKTFVKDORSMX-UHFFFAOYSA-N 0.000 claims 1
- ULGRACMCPGVEEK-UHFFFAOYSA-N 4-[1-(6-chloro-2,3-dihydro-1,4-benzodioxine-5-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC2=C1OCCO2 ULGRACMCPGVEEK-UHFFFAOYSA-N 0.000 claims 1
- ULWLHAACQVHNPR-UHFFFAOYSA-N 4-[1-[2-(dimethylamino)-6-methylbenzoyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CN(C)C1=CC=CC(C)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 ULWLHAACQVHNPR-UHFFFAOYSA-N 0.000 claims 1
- OEJKIMIEMMNCSZ-UHFFFAOYSA-N 4-[1-[2-chloro-4-(2-methoxyethoxy)-6-methylbenzoyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound ClC1=CC(OCCOC)=CC(C)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 OEJKIMIEMMNCSZ-UHFFFAOYSA-N 0.000 claims 1
- BIUDEVDBTBYDTN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-2-methylindol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC=CC=C2N(C(=O)C=2C(=CC=CC=2Cl)C(F)(F)F)C(C)=C1C1=CC=C(C(O)=O)C=C1F BIUDEVDBTBYDTN-UHFFFAOYSA-N 0.000 claims 1
- IIYPHUTYQFNHTA-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-formylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=C(C=O)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F IIYPHUTYQFNHTA-UHFFFAOYSA-N 0.000 claims 1
- LDWYFJQKADHORK-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-5-(methylamino)pyrrolo[2,3-c]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C1=2C=NC(NC)=CC=2C(C=2C(=CC(=CC=2)C(O)=O)F)=CN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F LDWYFJQKADHORK-UHFFFAOYSA-N 0.000 claims 1
- ZAFJKTHLHAQPER-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-5-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolo[2,3-c]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C1=2C=NC(NC(=O)OC(C)(C)C)=CC=2C(C=2C(=CC(=CC=2)C(O)=O)F)=CN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ZAFJKTHLHAQPER-UHFFFAOYSA-N 0.000 claims 1
- VWLWIRYLQWWKSU-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazinane-3-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=C(C=C11)C(=O)N2COCCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F VWLWIRYLQWWKSU-UHFFFAOYSA-N 0.000 claims 1
- MUIQMFMWWHLGBL-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazol-2-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2OC=CN=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F MUIQMFMWWHLGBL-UHFFFAOYSA-N 0.000 claims 1
- NTVUUWMYIXCQPR-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazole-2-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=C(C=C11)C(=O)C=2OC=CN=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F NTVUUWMYIXCQPR-UHFFFAOYSA-N 0.000 claims 1
- ZXYDLCCOBGDIMX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazolidine-3-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=C(C=C11)C(=O)N2COCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ZXYDLCCOBGDIMX-UHFFFAOYSA-N 0.000 claims 1
- SOLIBFAOUSRRQU-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-thiazol-4-yl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2N=CSC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F SOLIBFAOUSRRQU-UHFFFAOYSA-N 0.000 claims 1
- JJOYOICIYBODAK-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-thiazol-5-yl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2SC=NC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JJOYOICIYBODAK-UHFFFAOYSA-N 0.000 claims 1
- NACDHOZIQUKVIW-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1-methylimidazol-2-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound CN1C=CN=C1C1=CC=C(C(=NN2C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C=3C(=CC(=CC=3)C(O)=O)F)C2=C1 NACDHOZIQUKVIW-UHFFFAOYSA-N 0.000 claims 1
- FLOCZDVOIMRSCY-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1-methylimidazol-4-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound CN1C=NC(C=2C=C3N(C(=O)C=4C(=CC=CC=4Cl)C(F)(F)F)N=C(C3=CC=2)C=2C(=CC(=CC=2)C(O)=O)F)=C1 FLOCZDVOIMRSCY-UHFFFAOYSA-N 0.000 claims 1
- AOMVCSGXIXOKEM-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1-methylimidazol-4-yl)indazol-3-yl]benzoic acid Chemical compound CN1C=NC(C=2C=C3N(C(=O)C=4C(=CC=CC=4Cl)C(F)(F)F)N=C(C3=CC=2)C=2C=CC(=CC=2)C(O)=O)=C1 AOMVCSGXIXOKEM-UHFFFAOYSA-N 0.000 claims 1
- IDRHROXCDMIJRG-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1H-1,2,4-triazol-5-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2NN=CN=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F IDRHROXCDMIJRG-UHFFFAOYSA-N 0.000 claims 1
- YNUXZWMHLUWWNJ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2,5-dioxoimidazolidin-4-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C2C(NC(=O)N2)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F YNUXZWMHLUWWNJ-UHFFFAOYSA-N 0.000 claims 1
- DAEJUPFLIPARNN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-cyanophenyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2C(=CC=CC=2)C#N)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DAEJUPFLIPARNN-UHFFFAOYSA-N 0.000 claims 1
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- DBLOLXXKJOBMTA-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[5-(hydroxymethyl)-1,3-oxazol-2-yl]indazol-3-yl]-3-fluorobenzoic acid Chemical compound O1C(CO)=CN=C1C1=CC=C(C(=NN2C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C=3C(=CC(=CC=3)C(O)=O)F)C2=C1 DBLOLXXKJOBMTA-UHFFFAOYSA-N 0.000 claims 1
- MHRAJUWMBYVALM-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[cyclopropyl(hydroxy)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C=1N=C2C(C=3C(=CC(=CC=3)C(O)=O)F)=NN(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C2=CC=1C(O)C1CC1 MHRAJUWMBYVALM-UHFFFAOYSA-N 0.000 claims 1
- KPPSRVSRXSXIEN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[cyclopropyl(methyl)carbamoyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C=1N=C2C(C=3C(=CC(=CC=3)C(O)=O)F)=NN(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C2=CC=1C(=O)N(C)C1CC1 KPPSRVSRXSXIEN-UHFFFAOYSA-N 0.000 claims 1
- WDPHOVASCHHXHY-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[hydroxy(1,3-oxazol-2-yl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C=1N=C2C(C=3C(=CC(=CC=3)C(O)=O)F)=NN(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C2=CC=1C(O)C1=NC=CO1 WDPHOVASCHHXHY-UHFFFAOYSA-N 0.000 claims 1
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- GPEMWWDSWVCSHF-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[methyl(methylsulfonyl)amino]indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(N(C)S(C)(=O)=O)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F GPEMWWDSWVCSHF-UHFFFAOYSA-N 0.000 claims 1
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| WO2014026328A1 (fr) * | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | Composés d'indazole et d'indole à substitution 3-cyclohexényle en tant qu'inhibiteurs de rorgammat et leurs utilisations |
| WO2014026327A1 (fr) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | Composés d'acide benzoïque à substitution 4-hétéroaryle en tant qu'inhibiteurs de rorgammat et leurs utilisations |
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| WO2015139621A1 (fr) * | 2014-03-18 | 2015-09-24 | 北京韩美药品有限公司 | Acide benzoïque 4-hétéroaryle substitué ou composé de benzamides |
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| JP6728061B2 (ja) | 2014-05-05 | 2020-07-22 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγアゴニストとして用いるテトラヒドロキノリンスルホンアミド及び関連化合物ならびに疾患の治療 |
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| EP3242878B1 (fr) * | 2015-01-08 | 2020-10-14 | Impetis Biosciences Ltd. | Composés bicycliques, compositions et applications médicinales de ceux-ci |
| WO2016130818A1 (fr) * | 2015-02-11 | 2016-08-18 | Merck Sharp & Dohme Corp. | Composés pyrazole substitués utilisés en tant qu'inhibiteurs de rorgammat et utilisations desdits composés |
| EP3268087A4 (fr) | 2015-03-12 | 2018-08-29 | The Regents of the University of California | Méthodes de traitement du cancer par des inhibiteurs de ror gamma |
| CA2982847A1 (fr) | 2015-05-05 | 2016-11-10 | Lycera Corporation | Sulfonamides de dihydro-2h-benzo[b][1,4]oxazine et composes apparentes destines a etre utilises comme agonistes de ror.gamma. et pour le traitement de maladies |
| MX2017016134A (es) | 2015-06-11 | 2018-08-15 | Lycera Corp | Aril dihidro-2h-benzo[b][1,4]oxazina sulfonamida y compuestos relacionados para uso como agonistas de rory y el tratamiento de enfermedad. |
| ES2856931T3 (es) | 2015-08-05 | 2021-09-28 | Vitae Pharmaceuticals Llc | Moduladores de ROR-gamma |
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| WO2017075185A1 (fr) * | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Acides benzoïques à substitution hétéroaryle en tant qu'inhibiteurs de rorgammat et leurs utilisations |
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| KR102566924B1 (ko) * | 2016-07-29 | 2023-08-11 | 랩트 테라퓨틱스, 인크. | 케모카인 수용체 조절제 및 이의 용도 |
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| US7981888B2 (en) | 2007-04-16 | 2011-07-19 | Abbott Laboratories | 1-oxyalkyl-2-carboxyl-7-nonsubstituted indole derivatives |
| GB0708141D0 (en) | 2007-04-26 | 2007-06-06 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| AR067326A1 (es) | 2007-05-11 | 2009-10-07 | Novartis Ag | Imidazopiridinas y pirrolo -pirimidinas sustituidas como inhibidores de cinasa de lipido |
| WO2008153858A1 (fr) | 2007-06-05 | 2008-12-18 | Schering Corporation | Dérivés d'indazole polycyclique et leur utilisation en tant qu'inhibiteurs erk pour le traitement du cancer |
| US20100317863A1 (en) | 2007-07-25 | 2010-12-16 | Boehringer Ingelheim International Gmbh | Glucocorticoid Mimetics, Methods of Making Them, Pharmaceutical Compositions and Uses Thereof |
| EP2181710A1 (fr) | 2008-10-28 | 2010-05-05 | Phenex Pharmaceuticals AG | Ligands pour la modulation de l'activité du récepteur gamma orphelin (NR1F3) |
| WO2010050837A1 (fr) | 2008-10-28 | 2010-05-06 | Haskin Lev Yakovlevich | Installation éolienne |
| JP5930278B2 (ja) | 2008-11-25 | 2016-06-08 | ユニバーシティー オブ ロチェスター | Ｍｌｋ阻害剤および使用方法 |
| WO2010150837A1 (fr) | 2009-06-25 | 2010-12-29 | 第一三共株式会社 | Dérivé de l'indoline |
| US20130017188A1 (en) | 2009-07-31 | 2013-01-17 | The Brigham And Women's Hospital, Inc. | Modulation of sgk1 expression in th17 cells to modulate th17-mediated immune responses |
| JP2013514385A (ja) | 2009-12-18 | 2013-04-25 | ヤンセン ファーマシューティカ エヌ．ベー． | エストロゲン関連受容体αモジュレーターとしての置換アミノチアゾロンインダゾール |
| CN102883602B (zh) | 2010-02-16 | 2017-07-18 | Uwm研究基金会有限公司 | 降低细菌的毒力的方法 |
| US9290499B2 (en) | 2010-05-19 | 2016-03-22 | The University Of North Carolina At Chapel Hill | Pyrazolopyrimidine compounds for the treatment of cancer |
| EP2638014B1 (fr) * | 2010-11-08 | 2017-01-04 | Lycera Corporation | Tétrahydroquinolines et composés bicycliques associés n-sulphonylées pour l'inhibition de l'activité rorgamma et le traitement de maladies |
| KR20120063283A (ko) | 2010-12-07 | 2012-06-15 | 제일약품주식회사 | 신규한 피라졸로 피리딘 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| EP2655382B1 (fr) | 2010-12-22 | 2022-09-28 | Ludwig-Maximilians-Universität München | Complexes d'organozinc et procédés pour leur fabrication et leur utilisation |
| EP2487159A1 (fr) * | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | Inhibiteurs du RORgammaT |
| JP2014166961A (ja) | 2011-06-20 | 2014-09-11 | Dainippon Sumitomo Pharma Co Ltd | 新規インダゾール誘導体 |
| WO2014026327A1 (fr) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | Composés d'acide benzoïque à substitution 4-hétéroaryle en tant qu'inhibiteurs de rorgammat et leurs utilisations |
| WO2014026329A1 (fr) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | Composés d'indazole et d'indole n-alkylés en tant qu'inhibiteurs de rorgammat et leurs utilisations |
| WO2014026330A1 (fr) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | Composés 3-aminocycloalkyles en tant qu'inhibiteurs de rorgammat et leurs utilisations |
| WO2014026328A1 (fr) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | Composés d'indazole et d'indole à substitution 3-cyclohexényle en tant qu'inhibiteurs de rorgammat et leurs utilisations |
-
2012
- 2012-08-15 WO PCT/CN2012/080131 patent/WO2014026327A1/fr active Application Filing
-
2013
- 2013-08-14 EP EP13829282.6A patent/EP2884981B1/fr active Active
- 2013-08-14 KR KR1020157006322A patent/KR20150042266A/ko not_active Application Discontinuation
- 2013-08-14 US US14/421,048 patent/US9745265B2/en active Active
- 2013-08-14 MX MX2015001941A patent/MX2015001941A/es unknown
- 2013-08-14 AU AU2013302725A patent/AU2013302725A1/en not_active Abandoned
- 2013-08-14 JP JP2015527566A patent/JP6422438B2/ja not_active Expired - Fee Related
- 2013-08-14 CA CA2881688A patent/CA2881688A1/fr not_active Abandoned
- 2013-08-14 RU RU2015108894A patent/RU2015108894A/ru unknown
- 2013-08-14 BR BR112015003188A patent/BR112015003188A2/pt not_active IP Right Cessation
- 2013-08-14 WO PCT/US2013/054887 patent/WO2014028589A2/fr active Application Filing
-
2015
- 2015-02-12 IN IN1156DEN2015 patent/IN2015DN01156A/en unknown
-
2017
- 2017-07-12 US US15/647,437 patent/US10196354B2/en active Active
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